(3R,4S)-3-Hydroxy-4-phenylazetidin-2-one

(3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone is a stereodefined beta-lactam precursor used to construct the phenylisoserine side chain of taxanes. It supplies the required relative arrangement of hydroxyl and phenyl-bearing centers, while the strained lactam provides a ring-opening reaction handle. The hydroxy and nitrogen sites also permit the protection and acylation operations used in side-chain preparation.

This material is the specified chiral hydroxy beta-lactam, not a fully protected coupling reagent or a finished taxane. Its role is upstream of the complete C13 side-chain attachment sequence. Converting the hydroxyl and lactam nitrogen into the required protected derivatives allows the same stereochemical framework to enter different taxane synthetic routes without rebuilding the adjacent stereocenters.

Typical Applications

• Paclitaxel C13 side-chain synthesis: Used as a chiral precursor to phenylisoserine-derived side-chain intermediates, carrying the adjacent stereocenters needed for subsequent attachment to the taxane nucleus.
• Protected beta-lactam coupling-reagent preparation: Used in protection and N-acylation sequences that convert the hydroxy lactam into a route-specific taxane side-chain donor before ring-opening coupling.

Specifications

Specifications describe the standard grade. Tolerance, test method and documentation package are confirmed per order.